Meghan, Botswana & Fitting in an Engagement

Considering it’s August, there was certainly quite a bit of commentary this past weekend after news hit that Prince Harry took girlfriend Meghan Markle on a holiday in Africa for her birthday. And I say “Africa” because when the news first hit the location wasn’t specified beyond that, a fact that drew quite a bit of ire online.

We know now that the couple are in Botswana, a country with particular significance for Harry. He visited the country for the first time back in 1997, just months after the death of his mother, the late Princess of Wales. That trip, and his many subsequent visits to the larger continent, have resonated with Harry and he appears to enjoy a special connection with the place. While the Duke of Cambridge appears to have similar feelings for Africa – it played a role in the theme of his 21st birthday party and is where he proposed to his future wife in 2010 – Harry makes a point of visiting at least once a year, sometimes more.

Taking Meghan to the same location he went in those turbulent months in 1997 no doubt carries some extra significance this year – the 20th anniversary of Diana’s death. But even if the two aren’t joined in this case, it’s certainly not a bad sign for the relationship – quite the opposite.

And that of course begs the larger question: is Harry going to propose? The short answer is no one knows, but all signs point to yes…eventually. As for whether or not Harry will propose during this trip, there are three reasons why I think he might wait. (And one rather important reason why he he might not).

First, William and Kate were engaged in Kenya in 2010 and while obviously Botswana and Kenya are two very different countries, I think the stories would be seen as similar enough that it would be an annoying comparison that came up time and time again. Not a deal-breaker by any means, but it’s a factor worth considering.

Secondly, the fact that the media is well-aware that the couple are on this particular holiday – a key difference to William and Kate’s Kenya trip which no one was aware of at the time – indicates that there may be additional privacy concerns at play here.

And finally, timing, which is to say an engagement announcement is also a media event and as such there are some constraints on when it makes sense to start a public feeding frenzy. There are two particular events on the calendar that Harry and Meghan would need to work around, one of which is in late September when Harry hosts the third annual Invictus Games in Toronto and the other is the Queen and the Duke of Edinburgh’s 70th wedding anniversary in November which is expected to include public commemoration.

If we assume an announcement will occur this year, then it’s a fairly safe bet that it will happen before November. The choices are then August, September or October. The benefit of August is that it’s a quiet month and Harry and Meghan would be interrupting literally nothing; the downside, however, is that with the media having nothing else to focus on, it could end up becoming a ridiculous swirl of speculative stories – even more than expected.

September, before the Invictus Games, is certainly a possibility. This would allow Meghan to attend the games as Harry’s fiancee, however such an occurrence might also detract attention from a cause for which Harry is particularly passionate. I also disagree with some assertions that Meghan wouldn’t attend without an engagement – doing so is actually not that unprecedented based on how William and Kate handled their own relationship. I’m thinking specifically about Kate popping up at the Garter ceremony in 2008, a full 2.5 years before they were engaged. In any event, the main reason I can see for it not happening in September is that it’s the first official month of the Cambridges living in London and William working as a full-time Royal…however, splitting that attention might work in everyone’s favor.

As far as I know there’s nothing major on the calendar in October – the real question for an announcement happening this autumn is when they can fit in a wedding in 2018. Royal engagements are generally pretty short – six months tops.

November I would likely rule out as a possibility because of the Queen’s wedding anniversary, however there might be a nice sentimentality to Harry starting his marriage just as his grandparents are celebrating 70 years. The other reason I would rule out November is honestly because it’s the same month that William and Kate announced their engagement – again, the issue here is both drawing unnecessary comparisons and the scheduling of the wedding itself.

All that said, there are two compelling reasons why this August trip might be worth keeping an eye on. Taking Meghan to the very country that holds such a personal connection in the same month that Diana died might be exactly the sort of poetic full-circle moment Harry is looking for. It all comes down to the simple question of whether or not these two are ready to get married and that, unfortunately, I cannot answer.

This is all completely wild speculation and as you may be able to tell, it’s anyone’s guess at this point except for the simple fact that there’s a similar air of inevitability that surrounded William and Kate post-2007.

Another guess I’ll throw out there for no particular reason – I have a feeling Harry will pick St. Paul’s Cathedral over Westminster Abbey.